ChemicalBook CAS DataBase List DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE

DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE synthesis

2synthesis methods

Product Name:DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE
CAS Number:909391-56-6
Molecular formula:C15H24BNO2
Molecular Weight:261.17

124-40-3
510 suppliers
$18.00/100ml

(3-BROMOMETHYLPHENYL)BORONIC ACID PINACOL ESTER

214360-74-4
89 suppliers
$15.00/1g

DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE

909391-56-6
61 suppliers
$27.00/250mg

Yield: 77%

Reaction Conditions:

with potassium carbonate in acetonitrile at 20; for 16 h;

Steps:

XI
Procedure Xl INTERMEDIATE XI.1 : Dimethyl-r3-(4,4,5,5-tetramethyl-ri ,3,21-dioxaborolan-2- vDbenzyllamineTo a solution of 3-bromomethylphenyl boronic acid pinacol ester (Combi Block Inc., 297 mg, 1.0 mmol) in acetonitrile (5 ml.) was added dimethylamine (2M solution in methanol, EPO 2.0 mmol) followed by the addition of K₂CO₃ (691 nng, 5.0 mmol). The reaction mixture was stirred at room temperature for 16 h. Acetonitrile was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated NaHCO₃, dried (MgSO₄), filtered and the filtrate concentrated in vacuo to g ive dimethyl-[3-(4, 4, 5, 5-tetramethyl[1 , 3, 2]dioxaborolan-2-yl)benzyl]amine(INTERMEDIATE XU) as a viscous oil (200 mg, 0.77 mmol, 77%). Data for dimethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amine(INTERMEDIATE Xl.1): ¹H NMR (300 MHz, CD₃OD): δ 7.70 (m, 2H), 7.30-7.45 (m, 2H), 3.50 (s, 2H), 2.28 (s, 6H), 1.36 (s, 12H) ppm; MS (ESI), m/z: 262 ([M+H]⁺).

References:

AKZO NOBEL N.V.;PHARMACOPEIA DRUG DISCOVERY, INC. WO2006/95014, 2006, A1 Location in patent:Page/Page column 43-44

103-83-3 Synthesis

103-83-3
332 suppliers
$14.00/5g

25015-63-8
219 suppliers
$22.39/5G

878197-87-6 Synthesis

4-((N,N-DIMETHYLAMINO)METHYL)PHENYLBORONIC ACID PINACOL ESTER HYDROCHLORIDE

878197-87-6
63 suppliers
$45.00/100mg

909391-56-6
61 suppliers
$27.00/250mg

References

DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE Related Search:

3-(4-Methyl-1-piperazinylmethyl)benzeneboronic acid pinacol ester, 97% 4-[3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZYL]MORPHOLINE 1-[3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZYL]PIPERIDINE 3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER 1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]pyrrolidine